期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 10, 页码 3313-3317出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201509472
关键词
asymmetric catalysis; Diels-Alder reactions; organocatalysis; photochemistry; synthetic methods
资金
- ICIQ Foundation
- MINECO [CTQ2013-45938-P, SEV-2013-0319]
- CELLEX Foundation
- AGAUR [2014 SGR 1059]
- European Research Council [ERC 278541-ORGA-NAUT]
- Marie Curie COFUND action [2014-1-ICIQ-IPMP]
- CONACyT (Consejo Nacional de Ciencia y Tecnologia, Mexico) [237346]
- ICREA Funding Source: Custom
The photoenolization/Diels-Alder strategy offers straightforward access to synthetically valuable benzannulated carbocyclic products. This historical light-triggered process has never before succumbed to efforts to develop an enantioselective catalytic approach. Herein, we demonstrate how asymmetric organocatalysis provides simple yet effective catalytic tools to intercept photochemically generated hydroxy-o-quinodimethanes with high stereoselectivity. We used a chiral organic catalyst, derived from natural cinchona alkaloids, to activate maleimides toward highly stereoselective Diels-Alder reactions. An unconventional mechanism of stereocontrol is operative, wherein the organocatalyst is actively involved in both the photochemical pathway, by leveraging the formation of the reactive photoenol, and the stereoselectivity-defining event.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据